The Question That Changed My Life, With Ariel Upton

It was the first warm spring day in Chicago, a day Chicagoans look forward to like Christmas morning, when they can show their bare legs in the hot sun for the first time in months.

It was a glorious afternoon, + I had a lunch date with a family friend – a woman 40 years my senior – on a patio at a now closed trattoria on Wells Street.

I was 22 years old, on the cusp of college graduation, drowning in uncertainty around matters of the heart. I felt major pressure. From him, from others, + from myself, to make the “right” decision about a relationship that wasn’t serving me the way it should have.

I lacked confidence on how to act on what felt right to me, creating anxiety, uncertainty, + a healthy dose of self-doubt.

Thank god for that lunch.

That meal marks a pivotal moment in my developing years, because that was the day a family friend would become so much more. It was the beginning of what would become TODAY I DID IT RIGHT™ [www.todayididitright], + the start of a beautiful relationship with my life Guru, Betsy Tomlinson.

It was the day when a simple question, asked by a world-class listener + conversationalist [that would be BT], would change my life forever.

“What do you want?”

Betsy listened to me explain, + over-explain, the situation at hand, running through a seemingly never-ending list of pros + cons. She let me go on just long enough, before she stopped me dead in my tracks.

“Ariel, what do YOU want?”

In those five words, Betsy illuminated a corner of my mind that had been far too long in the dark. She introduced me to the concept of a choice, without advice or direction.

She never told me what she thought I should do.

She never brought it back to a previous experience of hers.

She never instructed.

Instead she gave me space to find my own answer, + the power to make a choice for myself.

The P-Word


In asking me what I wanted, Betsy showed me how to unlock a world where I could give myself permission to be the person I wanted to be. She gave me permission to take action, + actively pursue what it is I wanted, instead of sitting on the sidelines waiting for something to happen to me.

She gave me permission to own my choices, wants, + needs, ++ explore what living a right life looked like to me — instead of someone else. Even if that someone else was a previous version of me.

We so often find ourselves in worlds shaped by shoulds — imposed by society, + former versions of ourselves. We live by an imagined set of rules that dictates what we should think, wear, do, choose, believe, how we should behave, what we should care about, + the list of shoulds goes on, + on, + on.

It is only when we ask ourselves the question — what do YOU want? — that we have the opportunity to pursue a life that’s right for us.

Doing it right takes practice.

Every one of us experiences life in a different way.

Each of these experiences shapes our realities + the lenses we see the world through. With each of these experiences, + the time in between them, if we’re lucky enough, we change.

++ With every evolution of the self, what we want is going to change right along with it.

Asking, + answering the question — what do YOU want? — is far from a fixed exercise. It takes attention + discipline. It takes good old fashioned, blood, sweat, + tears [a lot of tears], + practice. It takes so much practice.

But, the more you practice shaping + expressing your wants, the better you’ll get at it. The more you practice doing the things that feel right to you, the better you’ll get at it. The more you practice silencing the shoulds, the closer to a right life for you, you’ll be.

++ Living a life that looks + feels right to you — what could be better than that?

— Ariel Upton of @TodayIDidItRight

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